Oilers insider drops mammoth Connor McDavid contract extension timeline update; ties it to Leon Draisaitl's wedding

Edmonton Oilers superstar Connor McDavid is entering into the final year of his eight-year, $100 million contract signed in 2017. Since the season ended with yet another heartbreaking Stanley Cup Final loss to the Florida Panthers, the Oilers and their superstar captain's camp are yet to engage in serious conversations regarding his future in Edmonton, which has some fans concerned.

Oilers insider Bob Stauffer dropped a mammoth update the timeline of Connor McDavid's contract extension on Oilers Now podcast. Stauffer also named some other key players who the Oilers will look to sign Mattias Ekholm, Jake Walman and Mac Gadowsky to new contracts.

"I still believe 100% that Connor McDavid will be extended in the off season by the Edmonton Oilers. I know there’s some people freaking out. I would think that maybe things (extension talks) might get percolating a bit, maybe after Leon Draisaitl’s wedding… in the first weekend of August" said Stauffer.

Leon Draisaitl is set to marry his partner Celeste Desjardins sometime in late July or early August, the couple have chosen to kept their wedding date private. They recently attended ex-Oiler Warren Foegele's marriage, with many current and former Oilers players in attendance. Connor McDavid and his wife Lauren were unable to attend the Foegele's marriage as Connor's older brother Cameron got married to his fiancee Sarah, at around the same time.

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Maple Leafs, every Original Six team will lineup for Connor McDavid if he hits free agency in 2026

Due to the lack of any advancements in Connor McDavid's contract extension talks with Oilers since the end of the season, NHL fans and media have been in a frenzy over his potential landing spot after the 2025-26 season, if he doesn't re-sign with the Oilers and becomes an unrestricted free agent.

On "The Steve Dangle Podcast", top insider Chris Johnston even considered the likeliness of McDavid joining his hometown team, the Toronto Maple Leafs in 2026 NHL free agency.

"(59:15) Of course, the Leafs — they've been nuts. But again, I think any of the Original Six teams are probably feeling like they could be in that mix if they're good enough," said Johnston.

So, according to Johnston, Connor McDavid may entertain the idea of joining any of the Original Six teams - Montreal Canadiens, Toronto Maple Leafs, Boston Bruins, New York Rangers, Chicago Blackhawks & Detroit Red Wings. He also adds that McDavid will hold all the cards in the negotiation with any of these teams, if it ever comes to down to leaving the Oilers, and any potential suitor would need to make him the highest paid player in the league.